The Teabuggers, those pesky kids charged with a federal felony for getting into Louisiana Senator Mary Landrieu's office under false pretences, see themselves as avant-garde Republican activists/humorists. So why aren't they, or any other right-wingers, funny?
On the surface it makes no sense. Why should political ideology affect humor when it doesn't affect earnings potential or charity-giving or most anything else?
But there is no good right-slanted Onion, or Daily Show or Bill Maher and no right-wing satirist who can nail liberals like Stephen Colbert nails conservatives. In 2007 Fox tried to launch a show to take on Comedy Central (despite Jon Stewart, in particular, sniping across political lines). The 1/2 Hour News Hour, marked by canned laughter, was described as "so heavy handed that it seems almost like self-parody," and was quickly cancelled.
If the Teabuggers, whose idea of hilarity is at the 'dress up funny' level of high-school skits, are the cutting edge, the new generation, then prospects are not looking good for the future either.
Maybe it's because absurdity and hypocrisy — staples of political humor — are far more prevalent on the right. If a family-values conservative gets caught with a wide-stance in an airport bathroom stall, or claims to be "hiking the Appalachian trail" when he's in fact schtupping the Argentinian woman, that is amusing. When liberals cheat or lie it tends to be far more mundane.
Or it might be that comedy, like journalism, is best when it comforts the afflicted and afflicts the comfortable. It's certainly partly built of empathy. ACORN, for all of its flaws, mainly works to give voice to the disenfranchised. Sure, you can trick them and sneakily edit your reporting and make them look silly, like O'Keefe did. But comforting the comfortable, and afflicting the afflicted just comes off as mean and nasty and smug. See: Dennis Miller and Ann Coulter.
Coulter and Miller were a sorority girl and and frat boy — Delta Gamma and Sigma Tau Gamma respectively. Which stands in contrast to the depressed, substance-abusing end of society that spawns many funny people. Richard Pryor made jokes about his cock looking like a foot from all the STDs he'd caught, and about setting himself on fire while smoking crack. We fear he would not be at all Sigma Tau Gamma material.
O'Keefe, from all we know about him, is more their stuff. He has grown up in a wealthy bubble, in slacks and blazers from the cradle up. That bubble is almost a prerequisite of conservatism — it's hard to be poor, or experience poverty, and still think poor people are just lazy. That is not to say privilege is a bar to humor or empathy, but if the toughest experience you've had is Juanita ironing an inadequate crease into your golf pants even though you've told her about this before, you may struggle to wield the comedy of universal experience.
Even if they have done some dumb, amusing things with their lives, conservatives are not given to self-deprecation, another shortcut to laughs. If Rush Limbaugh joked about Oxycontin, or Bill O'Reilly made falafel gags in the same way Letterman referenced his cheating, they might be more likeable.
Perhaps in the end it's just because, in the words of Stephen Colbert, "reality has a well-known liberal bias." Reality is funny. The rest is just wearing silly costumes for Andrew Breitbart.